Cherry had a long playing career in professional hockey, spent mostly in the American Hockey League, but he also had stops in several other minor leagues and played one game for the NHL's Boston Bruins in 1955, when he was called up during the playoffs. According to Cherry, a baseball injury suffered in the off season kept him from making the NHL.[3] He retired from hockey in 1970.[1] Cherry's younger brother, Dick Cherry was also a hockey player.

After the end of his playing career, Cherry struggled for a time as a Cadillac salesman and a construction worker. He worked as a painter earning $2 per hour.[4] In the middle of the 1971-72 season, Cherry became the coach of the American Hockey League's Rochester Americans. In his third season behind the bench, Cherry was voted the AHL's "Coach of the Year." After his three-year stint in Rochester, he was promoted to the NHL as head coach of the Boston Bruins, a team which was coming off a successful run of two Stanley Cups and three first-place finishes, but would see the departure of superstars Bobby Orr and Phil Esposito.

Cherry quickly developed a reputation for being an eccentric, flamboyant coach who strongly encouraged physical play among his players. It has been alleged he modelled the Bruins' playing style after that of his dog, Blue, a feisty bull terrier. This approach worked as the Bruins, known as the "lunch-pail gang", were one of the NHL's best teams during the latter half of the 1970s, capturing the division title three times from 1977-79. The Bruins were able to defeat the rough Philadelphia Flyers twice in the playoffs under Cherry's tenure. The Bruins made the Stanley Cup finals twice, both times losing to their arch-rivals, the Montreal Canadiens, in both 1977 and 1978. Cherry won the Jack Adams Award as NHL coach of the year in 1976.

Cherry, who had an uneasy relationship with Bruins General Manager Harry Sinden, was fired by the Bruins after a critical coaching mistake during a 1979 semi-final playoff series against the Canadiens. Up by a goal with less than two minutes left in the seventh game, the Bruins were penalized for having too many men on the ice. The Canadiens' Guy Lafleur scored the tying goal on the subsequent power play and ultimately won the game in overtime. Montreal went on to defeat the New York Rangers for their fourth straight Cup title.

Cherry went on to coach the Colorado Rockies the following season. Under his tenure, the Rockies adopted the motto "Come to the fights and watch a Rockies game break out!" This could be seen on billboards all over Denver in the 1979-80 season. Cherry's hiring as head coach immediately rejuvenated the ailing franchise's fortunes and many believe that if Cherry had stayed on, the Rockies would have remained in Denver (they instead relocated to New Jersey).

However, as he later admitted, his outspokenness and feuding with Rockies general manager Ray Miron did not endear Cherry to management.

Cherry was the part-owner and the former coach of the Ontario Hockey League's Mississauga IceDogs. The IceDogs' first three seasons were difficult ones with the team winning a total of 16 games. Cherry took over coaching duties in the fourth season. During Cherry's one season as head coach of the Mississauga IceDogs, the team managed 11 victories (only a slight improvement) and failed to make the playoffs for the fourth straight year.

In 1985, the first of a chain of franchised sports bars/restaurants bearing Don Cherry's name was opened in Hamilton. Cherry started as a partner in the operation and has more recently licensed his name to the chain without holding a significant ownership stake in the company. "Don Cherry's Sports Grill" has locations in Ontario, Nova Scotia, New Brunswick, Newfoundland and Labrador and Alberta. [1] As one of Canada's most recognizable and trusted faces (at least in some circles), Cherry has been an in-demand celebrity endorser for consumer products.

After his Rockies failed to qualify for the 1980 Stanley Cup playoffs, Cherry was hired as a studio analyst for CBC's playoff coverage that spring, working alongside host Dave Hodge. CBC hired him full-time in 1981 as a colour commentator, but he didn't last long in that role due to his tendency to openly cheer for one of the teams (especially the Boston Bruins or Toronto Maple Leafs). Instead, they created Coach's Corner, a segment that appeared in the first intermission on Hockey Night In Canada, with Dave Hodge. In 1987, Hodge was replaced by Ron MacLean, with whom Cherry has been teamed ever since. For several years he also hosted his own half-hour interview show, Don Cherry's Grapevine, which began on Hamilton's CHCH-TV in the 1980s before moving to TSN. His loud, outspoken nature became notorious, and his shows are described as "game analysis, cultural commentary and playful parrying with host Ron MacLean."[1]

Cherry's commentary is usually peppered with catch phrases like "All you kids out there...," unrestrained affection for his favorite players (including "Dougie," Kingston native Doug Gilmour, whom Cherry kissed on-air in a famous TV gag), and overall political incorrectness. Another trademark is his bull terrier Blue, originally a gift from the Bruins players. Some of the advice he gives is unchanging from year to year.

"Grapes" tends to have favourites among his many tidbits of advice. During the late nineties, virtually every week he would spend time exhorting the evils of placing one's stick in the line of fire (it inevitably caused deflections, and sometimes goals). Two other perennial favourites are the folly of the touch icing (a rule he blamed for the premature end to Pat Peake's career) and (several years ago) bemoaning the extremely sensitive rules about crease violation. He also spends time extolling true grit, such as when, in the 2000 playoff campaign, after sustaining a bone-shattering slapshot from Al MacInnis, a Phoenix winger crawled off the ice so that another could take his place. Usually at the end of the NHL season, his send off words in recent years have been about NHL prospects entering the NHL draft. His position is that unless a player is guaranteed to be selected in the first or second rounds, they should not physically attend the draft. The reason for this is that some players would be too disappointed if they are drafted later than expected, or worse, not at all.

Cherry returned to the news in May 2004 amid rumours that CBC would terminate his contract for Hockey Night in Canada. However, he re-signed with the network in July.

Branching out from his Hockey Night in Canada duties, Cherry began to release a series of videos called Don Cherry's Rock'em Sock'em Hockey in 1989. The 15th anniversary video was released in 2003, with a 'Best Of' released in 2005. Cherry returned to the "Coach's Corner" for the 2005-2006 NHL season - without the seven-second delay. For the 2007 Stanley Cup finals, NBC decided to feature Don Cherry in its intermission coverage, a rare appearance on American television. He was partnered with Brett Hull and it did not conflict with his usual role on CBC as he appeared on NBC during the second intermission.

Over his career on television, Cherry has generated significant controversy about both hockey and politics.In 2003 Cherry made controversial comments on his CBC segment in support of the 2003 invasion of Iraq. On the American radio program The Jim Rome Show the following week, he lashed out at CBC management for being anti-American.He was quick to criticize Pittsburgh Penguins' coach Michel Therrien for naming young Penguins' center Sidney Crosby a team alternate captain shortly after he was hired in 2005, with the simple statement: "He's an 18-year-old kid."

Don Cherry in recent years has become one of the biggest public personalities to endorse Cold FX cold medication. In the first year Don Cherry worked for the company, $1 from every bottle sold of COLD-fX was donated to Rose Cherry's Home for Kids.